I'm a staff writer for the Chicago Reader and a freelancer specializing in music, arts and pop culture journalism. My work has appeared in The A.V. Club, The Boston Phoenix, Esquire.com, Gapers Block, Newcity, PopMatters, Rock Sound, Spin.com, Thought Catalog, True/Slant, The Washington City Paper and Wired‘s Underwire blog.

But that’s not the plan he has in mind when I walk into his room at the Hotel Sax. He tells me he decided to stay at the hotel for me—or rather, for Forbes. Riff is no stranger to the Sax, as earlier this year he used his hotel room to film the video for “Mike Tyson,” a collaborative track with Illinois rappers Ghetty and Embassy. That’s also where he made a short video called ”Forbes List”: In it Riff trades his Texas drawl for a slightly British accent to play the role of Jody Highroller, his extremely wealthy alter-ego. Throughout the comedic “Forbes List” Riff’s Highroller criticizes the various items in his hotel room as if they’re beneath him, complaining that the water he ordered is “wet” when he ordered “dry” water, and sprinkling words like “poppyseed” and “posh” throughout his rant.

Riff Raff wants to make the Jody Highroller “Forbes List” narrative a reality by having me interview Mr. Highroller. I also have a plan—to talk to Riff about branding. That’s because Riff’s rap persona is partially made up of fragments of other well known brands that are re-imagined: His body is littered with tattoos of, among other things, MTV, BET, and WorldStarHipHop.com logos; his songs have titles like “Cookie Crisp,” “Jenny Craig,” and “Porche Cayenne“; and many of his recent videos show Riff wearing a gigantic chain of an Icee cup. That doesn’t seem to matter too much, as Riff sets his plan in motion as soon as I walk in the room. He’s going to ditch his clothes and put on a luxurious hotel robe. No, scratch that, two robes. His tour manager, Jackson Lagerlof, will escort me to to the “interview,” a task that will have him lead me to the living area in the hotel room, speak to Mr. Highroller from behind a curtain, draw back the curtain to reveal Highroller sitting in a bulky chair with its back to me, and, eventually, turn said chair around so that Mr. Highroller may speak to me. My part calls for me to walk back into the hallway and wait to film everything.

There’s a problem with Riff Raff’s idea: I didn’t bring a video camera. The issue reveals itself right after Lagerlof turns that large chair around and Riff notices my DSLR camera can’t take videos. Frustrated, Riff comes up with a new plan: We’ll re-do everything and I’ll use Lagerlof’s iPhone to shoot the interview.

I knew I might encounter some difficulty during the interview having read David Shapiro’s excellent profile on the rapper for Gawker. In that piece Shapiro traces Riff Raff’s public ascent from an outrageous contestant on a short-lived MTV reality show called From G’s to Gents to his current state as a somewhat viral pop persona: Along the way Shapiro attempts to dig up Riff’s back-story, a difficult task considering Riff has no interest in sharing his personal information with the world. In the days leading up to our meeting I made sure to come up with questions that would get the most out of Riff Raff.

I came prepared to interview Riff Raff: I don’t know what to do with Highroller. Flummoxed, I stumble over questions for a rather well-thought out character, or one that appears to have a book-long background. Riff appears to be having quite a bit of fun as Highroller, rolling out playful, comedic, and rich descriptions of what it’s like to be uber-rich and teaching me his various virtues.

Like what he hopes to accomplish in the following year: “I want to buy everything and sell it for half the price just to say I did community service. I don’t owe anyone anything.”

And his definition of the word “posh”: “Posh is anything below my level of doing things. For instance I’m on a private plane and there’s only five king-size beds, but I ordered seven, that’s posh. Walking to an airport and being around the common folk and the civilians, posh. Ordering a lobster in the actual restaurant instead of having it delivered to you fresh from the Pacific Ocean or the Sicilians, anything less than that, guess what it is?” [The answer: posh.]

And what he “demands” of Forbes: “I’d like to be on the cover of Forbes for 12 months straight. Yes, I think that would be very lagone of them if I wasn’t. Posh is what it would be if they didn’t have me on the cover.”

Though I’m unprepared to talk with Jody Highroller, the chat is reminiscent of I’ve come to love about Riff Riff’s music: It’s entertaining.

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